


Five More Minutes

by HyperKid



Category: Critical Role (Web Series)
Genre: Crack, Essek and Jester are fucking brats, F/M, Fluff, M/M, Multi, PWP, Things my brain does at 3am instead of sleeping, Voyeurism, cracky widojessek, lil snippets of smut, playing a game
Language: English
Status: Completed
Published: 2020-02-19
Updated: 2020-02-19
Packaged: 2021-02-19 03:29:09
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,106
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22804540
Author URL: https://archiveofourown.org/users/HyperKid/pseuds/HyperKid
Summary: Jester always seems to want attention right before Caleb has a lesson with Essek. Essek always seems to keep him late if he has later plans with Jester.
Relationships: Background PolyNein, Beau/Yasha/Jester/Caleb/Fjord/Caduceus, Caleb Widogast/Essek Thelyss, Caleb Widogast/Jester Lavorre, Shadowgast - Relationship, widojest
Comments: 10
Kudos: 257





	Five More Minutes

**Author's Note:**

> HK: Add this to the list of “things my brain did at 3am instead of sleeping”!   
> Mollymauk: That should be a tag.   
> HK: .... It’d be full of the weirdest and best things...   
> Mollymauk: Wouldn’t it be wonderful?   
> HK: ..... Be right back.   
> Mollymauk: It’ll be common enough to filter by.   
> HK: We can but hope! Cinderbrush isn’t yet.   
> Mollymauk: There there. You have plenty of your own stuff to write.   
> HK: And yet here I am with more 3am crack. 
> 
> WARNINGS!! Explicit sex and sexual language. Brat and sammy are BDSM terms for types of sub, sammy stands for Smart Ass Masochist (a sub who’ll act out on purpose for punishment) 
> 
> Disclaimer: I own nothing and no one but I’m calling dibs if they ever become available

By the time he realized it’s a game, they must have been playing it for months. Caleb couldn’t even begin to guess who’d started it or how long the other took to notice; for all he knew, Jester dared Essek outright and it had always been a game. 

Jester plays when he has an appointment to see Essek, when she knows the drow will be waiting for him in the library or their study. She’ll spill herself into Caleb’s arms, his bed, giggling and full of that mischief and laughter that he’s incapable of resisting. Pouted, pretty blue lips, a bat of lilac eyes, her hands skimming ever so gently across his body. 

He’s a little impressed he’s ever managed to resist her at all, and for a long time it meant Essek had the only point in the game. 

Because after a long, intense studying session, even if he’s supposed to be rejoining the Nein... how could he say no to the smile curling those dark grey lips, to that tilt of his chin that exposes the unmarked length of his neck? Magic is an irresistible lure to Caleb and it’s probably cheating that when Essek gets his turn, he’s already had an hour to wind the wizard up. 

Once Caleb realizes it’s a game, he makes sure to say no once though. To slip out, ignoring his erection to hurry back to his rooms and take himself in hand instead. 

To even the score. 

Jester and Essek might still be arguing over if that counts, since he still came before going to her side. Caleb couldn’t be completely sure how much they knew. 

But a discrete conversation with Fjord meant that he knows Essek scries on them sometimes, when he’s running late. It must be on Jester, Caleb’s amulet ensures that, but since Essek has to know who’s touching her, making her squirm and moan, means that it’s almost as good anyway. And he’s seen Jester cast Sending enough times to recognize it even while she’s riding him, broadcasting her little moans direct to her ears. 

Knows the spell well enough to know that Essek does it too, and that’s pretty much when it all clicked. 

The little shits. 

Not that Caleb ever let on that he knew; they might expect him to stop them. All it meant is that sometimes he had to suck a bite onto sweaty skin to hide a chuckle when one or the other telegraphs their victory. 

Preparing to leave early never worked, because if Jester had any inkling of when he was due to meet Essek, she was wonderfully skilled at drawing things out and distracting the wizard until he was late anyway. Sometimes he was pretty sure she’d made him even later purely on principle. 

Essek was at least more accommodating in that sense. He’d let Caleb schedule their lessons whenever the human pleased, so he could try slotting things in a little earlier than he had plans that involved his tiefling. 

But Essek would also occasionally drag out a lesson, snare Caleb’s attention with a casual description of a new spell that could be spun into “well, I suppose I could show you”. There’s nothing sexier to Caleb Widogast than watching magic swirl, shaped and controlled no matter how it’s done. And yeah, sometimes Essek’s down for a quickie, a hurried handjob rutting against the wall or swallowing Caleb to the root and sucking until he screams. And sometimes the Shadowhand takes his time. 

Draws things out. 

Bends Caleb over their study notes and fucks him slow, making him repeat what they covered just to prove he was paying attention. Caleb has always been good at those games. They’re some of his favourite tests. 

Fjord doesn’t seem to be an active player in this little contest. He tends to respect Caleb’s schedule, and if Caleb’s busy or got another appointment he won’t push. 

It might be part of the difference between his relationship to Essek and Jester’s? They seem to get along well enough, mostly by rarely actually speaking. Jester’s their primary contact to the drow, sunshine bright and always bursting with mischief. 

It might be because Fjord is much more concerned with seeming mature and adult, and about 90% of the game is just being a fucking brat to each other. A tiny smile always found its way to Caleb’s lips at that thought; there aren’t many better words to describe Essek in bed, and Jester’s more than capable of playing. Fjord... Caleb’s never seen Fjord brat. Even if he is a sammy. 

What it comes down to, though, is that Fjord never tries to make Caleb late and Essek never tries to make Caleb late for Fjord. The half orc might not even know the game is being played. Despite his curiosity, Caleb certainly wasn’t about to ask why. 

He might get an answer. 

Caduceus definitely isn’t playing, but if he was he’d be undefeated. There’s not a lover he’s taken who wouldn’t drop anything at the hint of his interest; it’s too rare to be passed up. Essek would certainly understand Caleb rescheduling a lesson to savour it. 

This game is just Essek and Jester, Caleb as their willing plaything to score points over one another. 

So now, his face pressed into the crook of Jester’s neck while his hips pump to grind his cock against her folds, he knows why there’s a smile curling the corners of her mouth. Not inside her yet, hands gripping plump ass cheeks to press them together, he kisses at her collarbone. Knows that since he’s asked her out to dinner, Essek will want to play too. 

Will probably want a little extra vengeance, he notes with a low laugh as he feels magic build, Jester’s moans suddenly much more vocal. 

“Oh... Caleb, yes... please, I need you to fuck me! Your cock feels soooo good, please, give it to me, fuck me long and hard!” 

It’s the most precise 25 words he’s ever heard her Send, and Essek’s answer must be profane from the giggles she tries to muffle in his hair. Licking his way down to her breasts to suck new marks, Caleb reaches down between them to ease himself into her. She’s so fucking wet that even without stretching her, he can slip in smoothly. 

Hot, tight, and absolutely incredible around him, Caleb shifts just enough that he can catch her g-spot with each thrust. Essek’s not exactly got a temper, but there’s a definite vindictive streak that Caleb knows will already be planning vengeance. 

Yeah, maybe he’s playing them both a little too. 

**Author's Note:**

> HK: This dynamic is ~the most fun~ you guys.


End file.
